I'm older now in my 40's. Since I was a teenager crossdressers have always turned me on. I've had a few. But the last couple of years I've been wanting to try to be the bottom. So I decided to go through it. I'm divorced so it was easy to get out. I ordered some slutty clothes on line with heels. I set a day to do it. I don't know anything about make up so I put an ad in the personals looking for someone to do my make up. When the day came it was a guy doing my make-up. He was straight atleast that's what he told me. I already had my outfit. I got dressed before he did my makeup. I wore a tight short black dress with sheer misty taupe pantyhose with 3 inch black heels. I had practiced the days before learning how to walk and I was pretty much good in them. When I came out the make up guy was speechless. Said I looked really good. As he did my make up he asked me what was the occasion. Told him the truth. I wanted to try being a women and get laid. He smiled and said 'really'? As he was doing my makeup I noticed he had a hard on . Didn't even try to hide it. He saw me look at it and said he was sorry but couldn't resist. That I look so sexy especially my legs in pantyhose. Told him thank you. He then told me if I needed someone to go with me he would. Told sure since this was my first time going out in public. After makeup and doing my hair(wig) i looked at my self and was Amazed. I even gave myself a hard on. As we were leaving I kept noticing him looking at my ass and legs. I'm a Hispanic so my legs are light brown and the pantyhose made them look good I have to admit. As we were driving I told him to go to an adult theater. We got there and I lost my nerve to go in. Started thinking about not knowing the guys. What if they had sexual transmitted diseases. I told the guy to just take me home. I gave him the reason and smiled. He put his hand on my thigh and squeezed. Said that he could give me what I want. His hand felt good on my thigh as he was caressing it. Told him sure why not. We get back and we go to my bedroom. I put on some music with a black light. He surprised me by coming up from behind me and pulled me to him. I felt his rock hard cock on my ass. Told me to pull it out and see what was in store for me. I do and was in shock. He must of been atleast 8 inches and thick. I told him hell no I wasn't putting that log in me. Pushed him off. He said he would be gentle. I kept saying no. But after a few beers that i drank that i had I was tipsy. He said atleast give him a blow job. I said sure. I was tipsy and horny. I got on my knees and was getting myself ready to try and blow him cause I've never done it before when he thrust his rock hard cock into my mouth. Immediately I began gagging not liking the way it happened. I was gagging so much that I couldn't even get half of his cock in my mouth. I told him he could have my ass if he stopped. He took my offer. After lubing about half the bottle in my ass and on his cock I layed on my back. I put my pantyhose legs on his shoulders. That was my fantasy to get fucked wearing pantyhose and my legs on the guys shoulders. He stuck a finger at first in my ass then 2. The first one felt good. The second Didn't at first . Then he said he was going in. Told him slowly. OMG! The head went in and it hurt like hell. The width was tearing me and it was only the head. He went in slowly and after about 15 20 minutes he finally got it all in. It hurt like he'll. It felt like there was a log inside of me. I could not only feel it inside me but I felt it in my stomach. But I only had to endure the pain for that little time. Because as he was working it in me little by little it was enough to get him to cum. My ass was so tight that he only went In and out 3 times and he busted his load in me and I felt the cum blast Inside me. And it hurt. As he pulled out of me cum drained out of me. End of part 1
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